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Reserve This Tour Get Detailed Itinerary

Price

US$ 550 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can’t run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info


Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

Save US$ 50 per person
Use our bike bags (panniers) instead of the luggage transfer
» more info

Dates

Any date from March 1 to October 31
3 Days, 2 Nights
Route Rating
Moderate: Two rides (19 and 9 miles) over hilly terrain.

Meet / Finish
Florence / San Gimignano
Highlights
  • Winery visit with guided wine and oil tasting
  • The Tuscan hill towns of San Gimignano and Certaldo.
  • Beautiful vistas of vineyards and olive groves
  • Peaceful country back roads

What's Included
  • All lodging (3 star hotels)
  • All breakfasts
  • One lunch
  • Winery visit and wine tasting
  • Luggage transfer from hotel to hotel
  • Private van transfer from Florence on day one
  • Two beautiful rides (18 and 10 miles). Extra miles available.
  • Use of high-end hybrid bicycle
  • Use of cell phone for emergencies

Cancellations: Terms and Conditions

» Tour Summary
» Map and Distances
» Hotels
» Photos
» Bicycles


Wineries and Castles
What if it rains?

On self-guided bike tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags. We provide our guests with a cell phone. You can call in the morning and make arrangements for a lift.


Why Self-Guided?
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates we take care of the details.

Winery and Castle Admission
All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.
Self-Guided Florence to San Gimignano Cycling Wineries and Castles
All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.
Albergaccio Machiavelli Winery, San Casciano
The Albergaccio Machiavelli winery was founded in 1693. Today they produce 300,000 bottles of wine, primarily Chianti Classico and Chianti Classico Riserva. Sangiovese, Canaiolo, and Pinot Nero grapes grow on 27 hectares of land. Nicolo’ Machiavelli wrote The Prince while living on this estate.
Palazzo Pretorio Castle, Certaldo Alto
(Entrance not included in tour price)
Palazzo Pretorio was originally the castle of the Conti Alberti family. Its facade is decorated with coats of arms. Inside is a museum with frescoes and Etruscan and Roman antiquities. The castle is the highest structure in Certaldo and offers amazing views of the surrounding countryside.